Your Dating Questions, Answered!

dating questions

She’s baaaack! Clara is back with her third and final post of this little series. I’m really hoping maybe she’ll come back in the New Year for another round of posts (or maybe join us on the podcast!). But in the meantime I love love loved reading her answers to your questions. So much good info in this post and be sure to check out post 1 (setting social media boundaries) and post 2 (meeting people IRL).

Hi friends! I can’t tell you how much I LOVED diving into your questions. It’s fascinating being on the receiving end and I really commend your vulnerability. I find regardless of who I talk to or work with, the same questions always come up. So know that you’re not alone. I couldn’t get to all of them but I tried to select the ones which covered the most ground. Also, I plan to cover all this content via my newsletter and Instagram in the coming weeks and months, so be sure to follow along over there if you’re interested.

Let’s dive in:

What should you ask about on a first date?

When clients pose questions like this, they’re generally looking for me to give them a script of exact questions to ask. What neighborhood do you live in? Where did you grow up? What do you do for work?

But instead, I ask them the following in return:

“What makes you feel you need to be told what to ask or what to say on a first date? What makes you think you could say the wrong thing?” And then they usually want to rip my head off! And I get it, I totally get it. Meeting someone new that you’re potentially attracted to can be hard and scary. Feeling nervous is totally normal. But the problem with all these scripts and what-to-text-back tips is that they both make us feel as if we’re doing something wrong by simply saying or doing what we feel, and they take us out of ourselves and the actual moment.

If you’re unsure of what to say on a first date, work with that! Saying something like “Aaah I have to admit these first dates always throw me a bit! It’s kind of weird to just start talking to a stranger.” When you open up, you give the person you’re with permission to do the same (in any context). Let it flow from there and remind yourself that you are ok, that you are whole, and you are deeply deserving of love.  And starting with “Hi! How was your day?” is perfectly fine, too.

Why do guys who ghost/say they’re not interested still watch my Instagram stories. I asked a guy about this and he said it doesn’t mean anything but I just don’t get it. If I’m not interested I don’t follow?

It’s important to take a step back from dating on this one and remind ourselves of something the internet has done – it’s allowed people to be a whole lot less kind to one another. I know Grace can attest to this. People comment and message horrific things they’d likely never say in person. They say things that are truly cruel and mean because they can remain more anonymous. Now, this guy isn’t being outwardly cruel to you, but I would put this behavior under the weird things the internet has allowed people to do (all of us included).

I don’t know this guy and I can’t speak for him saying it “didn’t mean anything,” but I can speak for myself. Recently, after a period of distancing myself from an old friend, I was honest about my behavior. I explained why I didn’t feel as connected to her. I apologized for my being avoidant and said I wasn’t sure how to do move forward but that I still thought fondly of our friendship and was open to trying again. That was several weeks ago. I’ve yet to hear back but in the meantime I’ve proceeded to watch all of her Instagram stories. I’m admittedly curious. She hasn’t written back and I’m not sure why, so I’ve taken to…following her every move? That’s not exactly kind, and it’s her right to not respond, and yet I’m still doing it.

My guess for this guy is that he’s not interested but likely bored and thus still curious. I think we’ve all done that thing where even if we’ve let someone go, we still wonder, “What are they up to?” The internet has allowed us to not just wonder. It’s especially unfair for the person on the receiving end, so if you find it to be upsetting or triggering, it is absolutely your right to block that person or to ask them to stop. It’s important for you to do what’s going to make you feel best.

Any tips for an almost divorced 30 y/o, starting over?

Yes! First off yay you for asking for help. I don’t know you but I sure am proud of you. It takes grit, courage, humility and a hell of a lot of kindness for yourself to start over, so kudos to you.

In my late 20s I ended a nearly seven year relationship, which in many ways felt like a marriage. We’d lived together for over three of those years, I was on his health insurance, he celebrated the holidays with my family, we were looking at property together – he was truly my best friend. It’s hard to sum up exactly how I healed myself, moved on, and started over, but here are three key things I did:

  1. I never pressured myself to “get out there.” I only dated when I wanted to. Yes, I was worried about my ‘timeline’ of marriage and babies, but I did my best to lessen that pressure and focus on the things in my life I could control. I went back to working for a big company to give myself more of a routine and some great health insurance. With that health insurance I went back to therapy and started sex therapy. I moved into a new apartment and decorated it exactly as I wanted to, aptly named the “princess pad.” I binge watched Friday Night Lights and started a yoga practice. I allowed myself to let it be hard, sad, scary, to question my decision, to wonder what if. Honestly, I did my best to accept the feeling I was experiencing versus fault myself for having the in the first place or try to force them away.
  2. I read a lot of self help, but the book I found to be most helpful at this particular was Elizabeth Lesser’s Broken Open: How Difficult Times Help Us Grow. Get yourself a copy and dive in.
  3. We set some strict social media boundaries, which I outlined in my first post.
  4. Lastly, I did my best to tune out other people’s thoughts and opinions. One of the key things that experience taught me was that there are only ever two people that know what the relationship was like: the two people in it. Some people told me I was brave for leaving, others questioned my decision. When I started dating again, some people applauded my efforts while others wondered how I could move on so quickly. Those people weren’t trying to be unkind or cause me angst, but their input wasn’t helpful. I did my best to brush it off and not seek it out in the first place.
How do you know the right time to start dating? Is it good to push yourself even though you don’t feel like it?

This is a GREAT question and one I feel very passionately about. I go into great detail on how to tell on one of the free downloads on my site. Grab the one called “My Most Important Question About Dating.”

To wait til the 3rd date (or longer?) Or not – does it make a difference?

I assume this question pertains to when you have sex with someone. There is only ever one answer to this question, and that is, whenever you want to – whenever you feel comfortable. That applies to kissing or any other form of intimacy, too. There was another question about when you DTR (define the relationship) when the other person wants to move faster and again, the answer is, whenever YOU my dear, are ready. All the bullshit out there that says if you sleep with him this early he’ll leave you. Or if you don’t sleep with him soon enough he’ll also leave you is just that, bullshit. There is no one right way. There are no true rules to dating. If this is the right person, you’re not going to do one singular thing to make the whole thing fall apart.

I just ended an 8 year relationship and I don’t have girlfriends. Help!

Again, kudos for reaching out for help! I think the more obvious ones are doings things like joining a yoga studio or book club, and joining the Stripe’s private FB group and pursuing a meet up (one of my favorite podcasts, Forever35) also does this via their FB group. But the thing I wanted to say that’s a little less obvious is this: often times, even despite our best efforts, when we get deep into a relationship some of our friendships can fall to the wayside. People we were once close to we may lose touch with. If there are some people like that in your life that you’d like to reconnect with but feel like you weren’t the best friend as of late if you feel brave enough, I recommend opening up about that.

A simple Facebook message or text like “Hey X – I know it’s been a while and I haven’t been the most preset friend as of late but it’d be really great to get together again. I saw you recently did XYZ – that looked so awesome! I’d love to treat you to coffee if you’re up to it.” Or however you want to phrase it. You could apply a similar tactic to someone who’s an acquaintance but who you’d like to get to know better. Something along the lines of “Hey X – so great seeing you at yoga! It’s been super helpful to me recently, being in the midst of a difficult breakup. If you ever want to grab a bite after class, let me know!”

I hope all of this was helpful! I work with women all over the world. So if you’re interested in dating and relationships support, I’d love to hear from you! Shoot me a message on Instagram or email at Dating can be hard, but not as hard as you think.

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  1. Katie:

    I LOVE this advice. Too often dating experts feel misogynistic to me, and by saying “men and this way and women are that way”, I think women end up in compromised, vulnerable positions. I love your stance on when to have sex with someone. The idea that a guy won’t like you if you sleep with them on the first date has always driven me bonkers. I wouldn’t want to date someone who was appalled that I wanted to sleep with them soon, and THATS why it wouldn’t work out! Thanks for bringing the feminist advice, we need more of it!

    12.7.18 Reply
    • Could not agree more. So happy you liked Clara’s post!

      12.9.18 Reply
    • Hi Katie – I’m so glad the responses came across that way. I’m really hoping to change the dialogue. I, too, find it to be really misogynistic and think that it ultimately puts women in a position of performing, placating and pleasing. Those things happen to also work against a successful relationship, so no one really wins!

      12.10.18 Reply
  2. Ah, I loved this! The range of questions covers everything. Particularly enjoyed the first question since I’m no longer in the dating scene, haha. 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    12.7.18 Reply
  3. cy:

    this is all great advice. I would add to the person that said , she just broke up and didn’t have any girlfriends, don’t be this person ever again! Everyone is busy, but you have to nurture your peeps! You never know when you are going to need each other! and friends make the world a better place and help you over a break up for sure.

    12.8.18 Reply